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Exploring Historic Massachusetts Harbors

by Deirdre Frost

Looking  for a quick seaside escape ? You’ll find plenty of choices along the Eastern seaboard. Two outstanding destinations combining historic cities and seaports that come to mind; Salem and Gloucester, Massachusetts. Both share a long maritime history, interwoven with whaling and the foundation of the United States. These coastal cities steeped in American history just 20 miles apart draw tourists from near and far.


Fort Pickering
Fort Pickering (Winter Island) lighthouse has protected ships sailing into Salem.

Salem has a rich history beginning with the indigenous people, the arrival of the first Europeans in 1626 and stretching into a dark period, culminating in the Salem witch trials.

Howard Street Cemetery
Howard Street Cemetery was one of the three cemeteries during the 1692 witch trials.






Strict religious practices, daily demanding physical labor and an inflexible moral code were the norms. These unusual times created strange phenomena stemming from the witch trials that provided fascinating encounters with apparitions , haunted graveyards and hanging sites.

Salem a vibrant coastal city.
Salem is a vibrant coastal city that retains its maritime heritage.



In Salem, it is possible to visibly contemplate the heady days when rich merchant traders and ship captains sailed the high seas to the far corners of the world.  Large merchant houses still stand including the old Custom House along the waterfront. Other indications of Salem’s glorious past are revealed at the Maritime National Historical Site where the tall ship, Friendship, is being remodeled.

The House of the Seven Gables

Nearby is the birthplace of Nathaniel Hawthorne  where he wrote The House of the Seven Gables based upon the aftermath of the Salem witch trials. According to one of the museum curators, Nathaniel Hawthorne wrote the book to exonerate his family’s involvement in condemning many of the accused for witchcraft.

Hawthorne's Birthplace
Nathaniel Hawthorne’s birthplace can be viewed in this historic preservation site.

The authentic buildings show daily life during that tumultuous period at the registered historic preservation site. The surrounding gardens are arranged in a beautiful floral design that borders the waterfront.

Landscaped Garden
This beautifully landscaped garden creates a peaceful setting at the Gables preservation site.

The Peabody Essex Museum

The Peabody Essex Museum also highlights Salem’s heritage with interesting displays of maritime history, art, and design. Featured in these exhibits are model ships, interactive scrimshaw exhibits, paintings and memorabilia depicting Salem’s glorious past. In particular, the museum displays some unusual items, such as exquisite diamond jewelry. Especially spellbinding is discovering how merchant ships would leave Salem for more than two year stints to the mysterious Orient to bring back exotic spices and luxury goods.

Salem has some of the finest examples of rich merchants original homes beautifully restored and in some cases, open to the public. Several architectural styles are present including many in the Federal style. On Chestnut Street, considered by many to be one of the most beautiful residential streets in the country, the Phillips House is a fine example of Federal style architecture with its tall ceilings and large windows.

The Salem Inn

The Salem Inn
The Salem Inn provides guests with the opportunity to experience staying in an historic home in Salem.

Close by is the historical Salem Inn that consists of accommodations in three former homes  of successful merchants:  Captain Nathaniel West, Captain George Curwen and John P. Peabody. Built in 1834 in the Federal architectural style, and the beautifully restored includes modern amenities and period furnishings.

In keeping with Covid considerations, the Inn has a touch-less check-in where guests can efficiently register with their smartphone prior to arrival.

The Inn’s central location is also most convenient to Salem’s historic sights, museums, and restaurants. Walking a short distance, we look no further than the Adriatic Restaurant & Bar for fresh Mediterranean seafood that proves an excellent choice to relax and dine in style.


Gloucester’s seafarers have overcome the restless waves on its coastline. for hundreds of years.

Coming to this historic seaside city evokes the image of a seafaring tradition that continues to make Gloucester a popular maritime destination.  Visitors can enjoy a pleasant sail on a beautiful classic schooner or search for whales out to sea.

Sailing on this magnificent Schooner provides marvelous views of Gloucester Harbor.

Schooner Thomas E. Lannon

Our Captain welcomes us aboard his 65-foot Schooner Thomas E. Lannon where we enjoy smooth sailing on a perfectly warm day with sea breezes.  As the boat glides through the water, the coastline is revealed and the distant Gloucester harbor front.

Captain Heath
Captain Heath’s Schooner the  Thomas E. Lannon provides smooth sailing around Gloucester Harbor.  





Some gulls and cormorants dive nearby into the waters, then surface with a caught fish that gleams in the sunlight. The sails gather more wind as the ship sails through the harbor. Passing the lighthouse, colonies of seabirds gather together on nearby solitary rocks. Large homes on the shoreline add to the fascinating scenery.

7 Seas Whale Watch

Later in the day we boarded a whale watching boat and headed for the open water, anticipating an exciting expedition in search of whales and other wildlife.

This humpback is quite a performer, slapping his fin as part of breaching.

As we move towards the Stellwagen Bank, a registered National Marine Sanctuary, we see a magnificent sea turtle swimming furtively on the sea surface, and then spot basking sharks as the boat heads towards the feeding bank. The ship moves into areas that show signs of humpback whales blowing in the distance.

Mother and daughter hunchbacks
Mother and daughter humpbacks swim in tandem.

Mother and daughter humpbacks swim in tandem. In one instance, visitors are treated to a delightful spectacle of two heavy-breathing mother and daughter humpbacks swimming side-by-side as they slice through the waters, creating excitement on deck.

In deeper water offshore, we watch for individual sperm whales, which suddenly appear catching their breath after long dives into the deep blue depths of the ocean.  Amanda, the naturalist on board, has everyone looking for bubbles, which indicate the whale’s presence and shortly, a whale breaks the surface.

The thrill is waiting for the whales to appear as nobody knows when the next one will surface.  The sightings are promising since the weather is bright and sunny and the water is remarkably smooth and calm.

The appearance of these humpbacks are astonishing as they entertain us with acrobatic movements and even breach a few times. During our time at sea, we spot different species including fin and minke whales that emerge from the water and then disappear from sight. The sheer excitement of seeing whales makes the time go quickly.

These agile performers like entertaining us — we just have to look up, and there they are – just offshore, blowing, breaching, lobtailing and fluking.


That evening, we enjoy dining at the Castle Manor Inn, on their terrace, where we have freshly-cooked seafood while overlooking the city and harbor of Gloucester.  The dishes proved to be well-prepared by an experienced chef who uses local sourced seafood and fresh produce.  The haddock and stuffed clams were one of his signature dishes. This was a perfect way to cap our enjoyable trip to the seaside harbor of Gloucester.

Cape Ann Motor Inn

Our stay at the Cape Ann Motor Inn provided excellent views of the wide beach at Long Beach. Some families were in deck chairs leisurely enjoying the bright sunshine while others were swimming and diving through the oncoming waves.

Long Beach
Long Beach is a favorite spot to relax and enjoy the seaside. Gloucester

With its prime beach location, the Inn is a favorite spot for locals and visitors alike.

Travel Essentials:


Where to stay:

The Salem Inn – Tel:  (978) 741-0680;

Where to eat:

Adriatic Restaurant & Bar – Tel: (978) 594-1832;

What to do:

The House of the Seven Gables – Tel: (978) 744-0991;

The Peabody Essex Museum – Tel: 978-745-9500;

Salem Trolley – Tel: (978) 744-5469;

Further information:

Destination Salem – Tel: (978) 741-3252;


Where to stay:

Cape Ann Motor Inn; Tel: (978) 281-2900;

Where to eat:                                                                                              Castle Manor Inn Restaurant – Tel: (978) 515-7386;

What to do:

Schooner Thomas E. Lannon; Tel: (978) 281-6634;

7 Seas Whale Watch – Tel: (978) 283-1776;

Further information:

Discover Gloucester – Tel: (978) 675-1818;

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